While I don't always agree with her, she is provocative, perceptive, honest, and kind, so it's a pleasure. She also regularly surprises me, which I really value. I recently chatted with her on instant messenger and the transcript is below and continues below the fold. We cover all sorts of topics.

First some words from Penelope about her new product, a "LinkedIn for Gen Y":

Gen Y needs a place to be found online by employers. Facebook is not appropriate for employers. For obvious reasons. And LinkedIn is great for employers. It's very professional. But the average age there is 40…. I think young professionals want to be known for their ideas. And there is not a way to be known for your ideas on LinkedIn. On LinkedIn you are known for what you have done in the past. On Brazen Careerist you can be known for your ideas. Brazen Careerist is a bunch of conversations about professional-related topics.

Ben: You blog about sex a lot. Why?

Penelope: I think about it all the time. So it comes into my head a lot when I'm writing blog posts. I sort of wonder why it doesn't come into more peoples' heads when they are writing blog posts.

Ben: People censor themselves.

Penelope: Yeah. Well. I censor myself too. I guess it's just we each have different types of self-censoring.

Ben: What do you censor? Like, what kinds of topics?

Penelope: I knew you were gonna ask that. And then I thought to myself: Be careful. Because this is not going to be a good post for my company if I write really a topic that I censor.

Ben: If you write about having abortions, being sexually abused, etc, it's hard to think of topics that you would NOT write about.

Penelope: I never say bad stuff about my ex-husband. I think it's trashy.

Ben: What are your theories on writing? What makes good writing?

Penelope: Being interesting. I know people think I write about sex, bulimia etc because it'll always be interesting. But you can find ten million blog posts about those topics that are painfully boring. Interesting isn't really about the topic. Any topic can be good or bad.

Ben: So being an interesting PERSON makes your writing more interesting.

Penelope: I think interesting sentences makes writing interesting. I think all people are interesting if you talk with them about the right stuff.

Ben: It doesn't mean they can write about things interestingly. All people are interesting to an extent; not all people are good writers

Penelope: Yes. Right. I think good writing takes tons and tons of practice. Also, I throw out a ton of blog posts. People think they just roll off my keyboard. They don't. Do you feel the same? that a good post takes tons of work?

Ben: Absolutely. For the quality that I aspire to, I am slow, and I often still don't meet that quality level.

Penelope: Sometimes I like reading your blog just because you make me feel good about craft. Because I can tell how much you care about craft and then I don't care so much that I spent two hours on the links to a post.

Ben: This is what I'm interested in. Craft. Having an interesting life is one thing. Being able to tell it interestingly requires some craftsmanship, or something.

Penelope: Oh. That's an important point. At some point in my life, I realized I could support myself just sitting at my kitchen table writing every day. But I worried that my life would not be complicated enough to be written about.

Ben: So your entrepreneurship gives you material?

Penelope: Yeah. I think that is true. Well, struggling to figure out how to do my life — in many aspects of life — gives me material. I couldn't be Dooce. At home with my family writing about being at home with my family. I need more drama….not that she doesn't have drama.

Ben: Alain de Botton has an interesting point on this. He says the professionalization of writing — novelists who write fiction full time — has made it so much fiction is disconnected from life as it's experienced by most people.

Penelope: Totally agree. And the French have this problem more than any other culture.

Ben: The "novelist on the side" — someone who's also holding down a day job, or did for most of his life — has more valuable insight.

Penelope: Yeah. I love Raymond Carver for this. His life was so hard, and he had no time to write. And he still did.

Ben: Does being a good writer help you in your entrepreneurship? Most people in business, I've found, are terrible writers. And they still do fine. Chris Yeh, of course, is an exception. Great writer. Great entrepreneur.

Penelope: I think I make more connections through being a good writer. Chris is a good example — I connect well with him, and often, through writing.

Ben: Yeah, in your case, your blog is so tied up in your business that I'm sure there are tons of benefits. Can I make an observation about what I think your favorite phrase is in blog posts?

Penelope: Yes.

Ben: "And you know what?" That rhetorical question.

Penelope: I love that. I love feeling like I'm talking with someone. You make me laugh. You are smart.

Ben: It makes your posts more conversational. "Conversation" gets thrown around a lot. You do it when talking about Brazen Careerist. “People are going to have conversations” etc etc. But it's not easy to have a good conversation in-person, let alone in writing.

Penelope: Yeah. That's true. I think you know from our lunches and dinners that I'm awkward to talk to. Which I think makes me really really want to connect through conversation online. And I think you can tell when someone really really wants to connect, and when it's BS conversation.

Ben: Changing gears. Why are so many Americans in therapy these days? Record numbers and dollars are going into therapy.

Penelope: Why are you not in therapy? It's so fun.

Ben: Because I can talk to you, Chris, etc.

Penelope: I am not your therapist, though. Friends are not therapists. Friends do give and take. You can just take from therapists. Which is why self-discovery goes so much faster in therapy. You should try it. You're so into experiences!

Ben: To play devil's advocate, I sometimes find I learn things about myself when I'm giving advice to others. That is, during the "give."

Penelope: Yeah. I find that, too.

Ben: I like the exchange.

Penelope: It's just different.

Ben: Will you ever NOT go to therapy, or is it life long?

Penelope: I take breaks. I left my last therapist when he told me dating the farmer is crazy and I need a guy who makes a lot of money.

Penelope: Each time I have asked one to coach me, I've thought it would be stupid, and I ended up learning a bit about myself. So I think the truth is probably that we can all learn a bit from a coach.

Ben: There are so many people giving advice these days. More than in the past? I'm guessing so. Again, therapy culture. "Life coach" is like "social entrepreneurship" – fancy phrases on age old concept

Penelope: Well, people understand that people who get coaching at work do better at work.

Ben: That doesn't prove a causal relationship to the coaching. People who seek out coaching are probably self-starters and will do better anyways

Penelope: Yeah. That's true. But I think probably people who are self-starters are good at getting mentors. My mentors give me great coaching. My therapists help me when I am too messed up to do what mentors recommend. Do you ever find yourself wanting to implement mentor advice but you can't?

Ben: Depends what "can't" means. Sometimes I disagree with the advice. Sometimes the mentor doesn't fully understand the situation, so I can't. Easier to nod and smile than explain everything.

Penelope: But sometimes I find that I don't have the self-knowledge I need to know if I want to do what the mentor recommends. Do you have that? You must. Yes?

Ben: Not all the time, but you never know in the moment. Only in hindsight. If you knew in the moment, by definition you would be able to handle it, right?

Penelope: Oh. That's right. True.

Ben: Self-knowledge: there are diminishing returns IMHO

Penelope: Well, it has to be inherently interesting. The ROI has to be process, not result, I think.

Ben: Good point.

Penelope: Blogging is totally that.

Ben: Yes

Penelope: Self-knowledge as process.

Ben: Do you enjoy writing your "five tips" posts as much as your more narrative posts?

Penelope: Oh. That's a good question. A lot of my five tips posts are the ones that have the most narrative. The one's where I wrote a story, with no point. And then, because I have to give career advice because I write a career advice blog, I turn it into five point. So really the five points ones are often ways for me to write whatever I want.

Ben: "because I have to give career advice because I write a career advice blog" – that's what I'm interested in. What % of posts do you write for this reason? I sometimes have to do this on entrepreneurship stuff. Like, "better appease those who are just reading for tech stuff"

Penelope: Do what?

Ben: Write posts "because this is a career advice blog so it better be structured as career advice.” And you wouldn't otherwise write it that way, if it was in some other medium or just a strictly personal blog

Penelope: In the history of writing, every piece of writing has a topic. It's a contract you have with the reader. You stay within the bounds of the reader's expectations, and if you do that, you can write in lots of surprises and the reader stays with you. Because surprises are fun. But if there's no contract, then there are no surprises. Every great piece of writing works this way. Bloggers with no topic. I don't know. I don't like that.

Ben: I don't have a "topic" — and I lose readership because of that.

Penelope: I know. Your topic, though, is the education of Ben.

Ben: I feel like sometimes your posts and Ramit's posts are written in a way that are maximally accessible and assume the lowest amount of knowledge about finance or careers or whatever. And you both have huge readerships.

Penelope: I try hard to only write posts that scare me. The part that scares me is interesting to me.

Ben: That's why your blog is so interesting to read.

Penelope: I find if the post doesn't scare me then I don't care about the comments and that's bad. It's dishonest conversation.

Ben: Are your readers smart? Are the comments usually smart?

Penelope: I learn a lot from the comments. I know after two or three if I was wrong. And I learn a lot about myself.

Ben: Interesting. If you write about yourself — as you do — you will learn about yourself I guess. I learn a lot about whatever topic I'm writing about, but rarely about myself per se I'm more risk averse on the blog.

Penelope: Why?

Ben: I'm more apt to see the negative

Penelope: Negative in what?

Ben: Negative consequences. I will take risks in in-person conversation or on the phone. Perhaps that's a sign of my lack of confidence in my writing. Or it has nothing to do with writing and everything to do with notions of privacy.

Penelope: I think you would be surprised how little negativity there is in being the phone you on your blog. I think the phone you is so interesting and your life would simply be more interesting if you let all of yourself show on your blog.

Ben: Right. You've said this before. That I’m more interesting in person than on the blog. You are about equally as interesting I think.

Penelope: I can't decide if I should have you cut that part. This is the part of me that is self-censoring, I guess.

Ben: We can talk about it over email.

Penelope: I am not sure if people know how much I care about what they think.

Ben: I basically think that everybody care a lot about what everybody thinks. And anyone who claims otherwise is lying. Look at the letters to the editor in a book review section. Hugely famous authors writing in to complain about the smallest of small insults in a review. Maybe it's just that writers have thin skin.

Penelope: I'm not sure. I like to think I don't have thin skin. I mean, the commenters on my blog rip me to shreds, and I'm okay. So I don't know.

Ben: "Okay" is relative. Who knows how you'd be if you didn't put yourself out there as much? Or if you just sent out those posts on a private email list to 50 people who would offer mature, constructive feedback. Have you thought about doing something like that?

Penelope: I like hearing from people I don't know. New people. I like the range of people I meet.

Ben: Why? They don't know you.

Penelope: I don't even know me.

Ben: That's a therapy kind of statement. Do you value their feedback equally?

Penelope: I judge each piece of feedback, whether from a therapist I pay for, or from someone one the blog.

Ben: Equally, regardless of their intimacy to the situation or you?

Penelope: Yeah.

Ben: Wow.

Penelope: I find that I am able to have the best view of the people I am least close to.

Ben: So random dumbass Joe gives you feedback on your business plan and you treat it equally as what Chris would tell you?

Penelope: Business plan is not personal. There are rules. Chris is great with rules.

Ben: Life stuff is the same. Has nothing to with “rules” IMHO

Penelope: I think you are a feedback snob.

Ben: I'm an elitist, yes. I do not believe the homeless person has as valuable feedback as Chris or you.

Penelope: But a homeless person knows stuff that only homeless people know.

Ben: Yes. He knows what it's like to be a homeless person. But that's probably it.

Penelope: Just get their feedback for stuff they know.

Ben: Pretty narrow. I'm not that interested in what it's like to be a homeless person.

Penelope: He knows what it's like to be lonely. To hit bottom. To ask for help. To be looked down on.

Ben: You’re reaching. I wish life were so romantic where homeless people could articulate these profundities.

Penelope: Oh my god. This is so callus that I am laughing. Okay. This is what I think. That I know stuff because I have had really hard times in my life, and people devalue what I learned from that because most people who have gone through what I've gone through are the underclass. So I guess I'm just saying that I am careful to not devalue it in other people.

Ben: What do you mean "underclass"?

Penelope: I don't really know. I guess the people you think are not good enough to give you advice.

Ben: Let's use a concrete example. Homeless person Joe. Using drugs. On the street for 5 years. They're all over San Francisco. Would you ask him for feedback on your business plan? No. Maybe you'd talk deep thoughts about what it's like to be lonely. Their knowledge is more likely specialized

Penelope: Okay. That's a good point. That advice is specialized.

Ben: So if I'm going to have a few people I go to for advice, generally, I'd rather have someone w/ broader knowledge and the analytical ability to generalize appropriately or intuit appropriately based on the world I live in.

Penelope: We each give advice in our areas we’re good at. But the blog gives me the ability to go to a large group of people. I can't get past the snobbery piece.

Ben: Because he's someone not of a white collar profession who you interact w/ a lot, and have said you learn a lot from. And I would say, it's probably pretty specialized to farming, no? But also: farming is HUGELY complex and sophisticated and farmers tend to be very smart. So it's not at all like the drug addict homeless person. Maybe farming used to be quaint but as I understand it, between the weather calculations, technology, etc, it's sophisticated stuff

Penelope: I like that you know me well. So I was gonna say that the farmer has little knowledge of stuff beyond farming. But he is so so smart, that he keeps me interested. So I was thinking that maybe advice is interesting to me if it feels smart. Like, there is something I didn't think of. I am a sucker for a new idea. So in that way, I guess I'm like you.

Ben: Can the farmer give you advice on your life? Do you value it?

Penelope: Yeah. I have to tell him what's going on. But he can see it.

Ben: But then, you tend to be not very discriminatory when it comes to advice. You take it from random blog commenters.

Penelope: But I don't need him for advice. I need him to care about me. So the bar is lower for advice.

Ben: That's why romance kind of complicates things. I think though in general I try to defend the word "elitist" and I don't like how the frequently the "snobbery" charge is leveled at anyone who veers into that domain.

Penelope: I understand the difference. Your elitism makes me nervous. I'm not really sure why. Why can't we sometimes be stupid? I cannot be so smart all the time.

Ben: I don't see the connection.

Penelope: You are so hard to keep up with.

Ben: Some of the smartest people I know have huge uncertainties. We all do, right? I do.

Penelope: It's not uncertainty. It's letting my guard down and being stupid. Sometimes that's nice to do. I am unsure how I could do that with you. I would lose you.

Ben: Yeah, every time you self-bash [though not sure that’s what you mean by “being stupid”], I get annoyed!

Penelope: Haha. okay.

Ben: I don't see the fun or pleasure in "being stupid". Letting guard down is another thing: being relaxed, having fun, etc. All good!

Penelope: Okay. I don't mean stupid. I do not think I'm stupid. I think you know that. But I think that you wear me out. Do we always get to this point? Where you wear me out?

Ben: Don't know.

Penelope: Oh this. That I get tired of ideas and have to be more personal. That's what happens. And then we always get to this point. And then I demand that you talk about something really personal with me.

Penelope: Yeah. I can't really tell what you are feeling if we are doing ideas.

Ben: You have a lot of practice with personal. And your candor can be intimidating

Penelope: I know. Think that is part of our pattern. We get to this point and then you tell me that.

Ben: yep

Penelope: I am actually really surprised at how much ground we have covered together. Like, to have these patterns.

Ben: Not sure if it's a good thing or not but it's true

Penelope: It's sort of a substitute for personal conversations. We have dances around personal conversations. So we know the dance well.

Ben: Conversations with you quickly turn meta.

Penelope: they do?

Ben: It's hard to directly talk about something — you are more interested in talking about what we're talking about. You like meta. Look at your review of Ramit's book. Why didn't you just review it instead of making it about how a friend asked you to review it?

Penelope: I don't really know how to write about a book. I only know how to write about myself.

Ben: I don't buy that.

Penelope: Well. I know how to write about a book, but it's not as interesting to me. I wanted to have fun.

It goes back to having to write about careers. I still write to have fun

Ben: Is anything as interesting as yourself?

Penelope: Um. You are very interesting to me.

Ben: Ha

Penelope: The number of people I talk with as much as you is zero. I don’t talk with the farmer on the phone or in email. I don't really talk with people.

Ben: Some would look at the last few lines and say you're narcissistic. Is that true? Is that a bad thing?

Penelope: I try to not be that.

Ben: What does it even mean, anyway?

Penelope: I have been looking in the dsm because so many people say that on my blog. And I think that the difference between a narcissist and someone with aspergers is do they want to be the center of attention or not. And I hate having attention. i am almost never with more than one person at a time because i hate attention.

Ben: Oh ok. That makes sense

Penelope: thank you. Good example of how I learned about myself from the commenters.

Ben: Do you read many books?

Penelope: yes. sort of

Ben: but you don't like writing about them?

Penelope: I read novels and poetry. Sometimes I put a poem on the blog and people hate it. I watch your sidebar to see what you read. I think you have a lot of time to read and maybe need to spend more time having personal conversations.

Ben: Maybe. Easier to abandon a book if it's uninteresting

Penelope: Nice.

Ben: Quasi joking! Per prior part of the conversation.

Penelope: Let's go to the girlfriend topic. I think this is part of our dance. I ask prying girlfriend questions. You give short, unsatisfying answers. Let's do that now.

Ben: Shoot.

Penelope: Do you have one?

Ben: No.

Penelope: Are you just doing one night stands with women whose husbands are out of town?

Ben: Please.

Penelope: That was a fast dance. Usually we do not get to the end that fast.

Fascinating conversation. Both of your personalities really come through, and I can even here the exact way you intone, “Indeed.”

Also glad that I came up a couple of times. Logically, we should now do chats with you and me, and me and Penelope, before climaxing with a threeway (chat, that is). Which sounds awkward. Which probably means Penelope would love it.

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Penelope’s blog is fascinating and I value her honesty and openness. It’s so rare to see someone write so well and candidly on a variety of topics including bulimia, her childhood and careers so candidly.

I agree with Mike – this would’ve been a great Think TV episode! A possibility in the future or another time?

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Penelope’s written about how terrible her husband is at giving head, how it was a mistake for her to have married a man who is no good at it. For her to say “I never say bad things about my ex-husband” is absurd. On the other hand, she’s said in the blog that she shows her posts to the people she writes about in them, and they have the right to edit. If this is the case, the guy’s merely a masochist.

Her recent revelations about her struggle with Asperger’s put a great deal of her behavior — at least as she describes it in her blog — in a new and useful light.

Re-think the value of elitism. It’s usually a bad thing. Paul Wolfowitz should not have been allowed to make decisions about Iraq. His status as a member of the elite hurt our country, as did McNamarra in his time. Elitism affords privilege that is both unearned and over-valued.

I’m a big fan of yours, so go easy on me, young fella.

Dan Owen

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Totally agreed. And yes, I normally would: but go check out that post I referenced. The last thing I want is Penelope deciding to come after ME the way (or worse) she did after that guy. Dellifield is now permanently marred in Google by that episode.

Anonymity has its purposes in preventing retribution: secret ballots for example, or cases like this one, when you’re dealing with the deranged.

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I had never read Penelope’s blog before but I see why it’s popular – her narcissism is the perfect complement for our voyeurism. I found myself being sucked in by it and had to stop myself. Turns out I agree with a lot of what she has to say, and I like her writing. Yes, she’s a little wacked, but you don’t have to read very far or think very hard to understand why.

I don’t really get the Brazen Careerist website, though. Ideas matter, but so does getting things done. And the best ideas usually, though not always, come from people who really know a field, i.e., they have experience. Thus for people early in their careers, this site seems like a really good opportunity to show that you’re a novice and not aware of the things that have been tried but don’t work. Furthermore, if you have a genuinely novel and valuable idea, shouldn’t you be pursuing it rather than blabbing about it on a social network?

What am I missing?

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A final thought: while you may not seek the advice of homeless person, you may benefit from their perspective, even in a difficult, notionally intellectual topic. Think health care.

And I agree with DaveJ. I read some blogs by Gen Y types, but I’m generally unimpressed with their alleged insight and turned off by their collective specialness.

The best ones, save perhaps Ben, don’t write about themselves or their generation at all, but instead about a topic in which you can educate yourself without direct experience. Conor Friedersdorf comes to mind, but he’s obviously a writer first, job seeker second.

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However, if she is “the most influential career blogger” as you said, we have a problem.

Her advice is too extreme, too black-white, and overly generalized. She likes to say the “Y-Generation” is different, and then gave out generation-specific advice. In reality, those are things Y-generation likes to hear, but not necessarily the appropriate advice.

I’m a little bit older than the Y-generation. I guess I can call myself the X-generation. 🙂 When I came out of school, the magazine Fast Company just came out. It started promoting ideas such as the “old economy is dead”, “the x-generation didn’t work for anyone”, etc. Those are the same things Penelope is promoting in her “career advice”. Ten years later, after two recessions, the workplace changed, but had not changed as much as the so-called career pundits describd.

I’ve been reading your blog for years, Ben. Your friend Marty is a great career counselor (although I don’t agree with some of the stuff he said.) But, Penelope is an example of extreme and dangerous career advice.

Read her blog for entertainment, not career insights.

Peace.

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I enjoyed this. I’ve also done some higher-order learning from it, since I’m preparing a few text-based interviews of my own as well. So, I can, y’know rip your technique off employ valuable lessons from your example.

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The reason that all the stuff gen Y does sounds like what gen X what talking about is because it is. The difference is that gen X was too small to force change in the workplace when we Xers were in their 20s. Gen Y is much bigger, so they can ask for the same stuff Xers wanted, and gen Y gets it.

Ben hates the generational stuff I talk about. So having the opportunity to slip some in in the comments section is a treat 🙂

Penelope

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Sorry Ben,
No, I think those are terms of the moment for those years in general. Just commenting on how I never heard of Asperger’s before this year,now it is everywhere, on every cover, articles all over the place…

Much like elegant is what every programmer wants their work described as in ’08, much as every business wanted to talk up their ‘green’ side in ’07.

Yeah, pretty clearly DSM is available online, which I should have anticipated…I only encountered the DSM in psych classes, have never considered actually referencing it for myself/others I know.

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Thanks for your comments, Penelope. I definitely hope that Y-generation can make things happen, bring positive changes to workplace.

Just like the old saying “when you’re young, you’re democrat. When you become older, you become republican”, I think y-generation (if there is such a thing) will outgrow themselves, and possibly “sold out” just like the previous generations. 🙂

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One of many problems is that if your approach to solving a problem or accomplishing a goal is to first ask, “Which member of the elite should I pick to solve this?” you end up with Paul Wolfowitz versus Brent Scowcroft kinds of choices. You might think of this as a Best and Brightest problem. If you pick wrong, you’re screwed.

It’s important to frame the problem correctly and not take a shortcut to a solution by using someone’s elite status as a filter. In a country with the kind of human capital resources we have, it’s neither necessary or smart.

There’s hardly a way you can frame a problem that the best answer would be “Sarah Palin,” although if your goal is to torpedo health care reform it’s not a bad solution. Ben’s told us that he’s leaving the solution to this problem to the elite, though, so it’s not worth talking about here.

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I just found Penelope’s blog quite recently and through her found yours.

I thought the IM conversation was amazing! I wasn’t aware how many people think Penelope is “wack” or really understand it. She just seems to be honestly expressing herself.

Anyways, I found both of you in the conversation to be both honest and interesting, and I think that is a very rare combination. I also liked the part about your experiences blogging. I just started recently, and I find it hard to find my voice and at times scary.

Lisa

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